Investigation of the histamine H3 receptor binding site. Design and synthesis of hybrid agonists with a lipophilic side chain

Journal of Medicinal Chemistry

Volumn 53, Issue 17, 2010, Pages 6445-6456

  Ishikawa, Makoto ^a   Watanabe, Takashi ^a   Kudo, Toshiaki ^a   Yokoyama, Fumikazu ^a   Yamauchi, Miki ^a   Kato, Kazuhiko ^a   Kakui, Nobukazu ^a   Sato, Yasuo ^a  

^a MEIJI SEIKA KAISHA LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 (TERT BUTOXYCARBONYL) 4 [2 HYDROXY (1 TRITYL 1H IMIDAZOL 4 YL)ETHYL]PIPERIDINE; 2 (1 TOSYL 1H IMIDAZOL 4 YL) 3 (4 TRIFLUOROMETHYLPHENYLTHIO) 1 PROPANOL; 2 (1H IMIDAZOL 4 YL) N METHYL 3 [4 (TRIFLUOROMETHYL)PHENYLTHIO]PROPANE 1 AMINE; 2 [1 (TERT BUTOXYCARBONYL)PIPERIDIN 4 YL] 2 (1 TRITYL 1H IMIDAZOL 4 YL)ACETIC ACID; 3 (4 TERT BUTYLPHENYLTHIO) 2 (1 TOSYL 1H IMIDAZOL 4 YL) 1 PROPANOL; 3 (4 TERT BUTYLPHENYLTHIO) 2 (1H IMIDAZOL 4 YL) N METHYLPROPANE 1 AMINE; 4 [1 (1H IMIDAZOL 4 YL) 2 [4 (TRIFLUOROMETHYL)PHENYLTHIO]ETHYL]PIPERIDINE; 4 [2 (4 TERT BUTYLPHENYLTHIO) 1 (1H IMIDAZOL 4 YL)ETHYL]PIPERIDIN; 4 [2 (4 TERT BUTYLPHENYLTHIO) 1 (PYRIDINE 2 YL)ETHYL] N,N DIMETHYL 1H IMIDAZOLE 1 SULFONAMIDE; 4 [2 (4 TERT BUTYLPHENYLTHIO) 1 (PYRIDINE 3 YL)ETHYL] N,N DIMETHYL 1H IMIDAZOLE 1 SULFONAMIDE; 4 [2 (4' TERT BUTYLPHENYLTHIO)ETHYL] 1H IMIDAZOLE; 4 [2 HYDROXY 1 (PYRIDINE 2 YL)ETHY] N,N DIMETHYL 1H IMIDAZOLE 1 SULFONAMIDE; 4 [2 HYDROXY 1 (PYRIDINE 3 YL)ETHY] N,N DIMETHYL 1H IMIDAZOLE 1 SULFONAMIDE; 4 [2 HYDROXY 1 (PYRIDINE 4 YL)ETHY] N,N DIMETHYL 1H IMIDAZOLE 1 SULFONAMIDE; HISTAMINE H3 RECEPTOR AGONIST; METHYL 2 (1 TOSYL 1H IMIDAZOL 4 YL) 3 [4 (TRIFLUOROMETHYL)PHENYLTHIO]PROPANOATE; METHYL 3 (4 TERT BUTYLPHENYLTHIO) 2 (1 TOSYL 1H IMIDAZOL 4 YL)PROPANOATE; N 3 (4 TERT BUTYLPHENYLTHIO) 2 (1 TOSYL 1H IMIDAZOL 4 YL)PROPYL N METHYL 2 NITROBENZENSULFONAMIDE; N METHYL N 3 (4 TRIFLUOROMETHYLPHENYLTHIO) 2 (1 TOSYL 1H IMIDAZOL 4 YL)PROPYL 2 NITROBENZENSULFONAMIDE; N,N DIMETHYL 4 [1 (PYRIDINE 2 YL) 2 (4 TRIFLUOROMETHYLPHENYLTHIO)ETHYL] 1H IMIDAZOLE 1 SULFONAMIDE; N,N DIMETHYL 4 [1 (PYRIDINE 3 YL) 2 (4 TRIFLUOROMETHYLPHENYLTHIO)ETHYL] 1H IMIDAZOLE 1 SULFONAMIDE; N,N DIMETHYL 4 [1 (PYRIDINE 4 YL) 2 (4 TRIFLUOROMETHYLPHENYLTHIO)ETHYL] 1H IMIDAZOLE 1 SULFONAMIDE; N,N DIMETHYL 4 [2 (PYRIDIN 2 YL)OXIRANE 2 YL] 1H IMIDAZOLE 1 SULFONAMIDE; N,N DIMETHYL 4 [2 (PYRIDIN 3 YL)OXIRANE 2 YL] 1H IMIDAZOLE 1 SULFONAMIDE; N,N DIMETHYL 4 [2 (PYRIDIN 3 YL)OXIRANE 4 YL] 1H IMIDAZOLE 1 SULFONAMIDE; TERT BUTYL (2 NITROPHENYL)SULFONYL[2 (1 TOSYL 1H IMIDAZOL 4 YL) 3 [4 (TRIFLUOROMETHYL)PHENYLTHIO]PROPYL]CARBAMATE; TERT BUTYL 4 [CYANO(1 TRITYL 1H IMIDAZOL 4 YL)METHYL]PIPERIDINE 1 CARBOXYLATE; TERT BUTYL 4 [CYANO(1H IMIDAZOL 4 YL)METHYLENE]PIPERIDINE 1 CARBOXYLATE; TERT BUTYL [3 (4 TERT BUTYLPHENYLTHIO) 2 (1 TOSYL 1H IMIDAZOL 4 YL)PROPYL] (2 NITROPHENYLSULFONYL)CARBAMATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; BINDING AFFINITY; BINDING SITE; DRUG ACTIVITY; DRUG DESIGN; DRUG PROTEIN BINDING; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HYDROPHOBICITY; LIPOPHILICITY;

ANIMALS; BINDING SITES; CHO CELLS; CRICETINAE; CRICETULUS; DRUG DESIGN; HISTAMINE AGONISTS; HUMANS; IMIDAZOLES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PIPERIDINES; PYRIDINES; RADIOLIGAND ASSAY; RECEPTORS, HISTAMINE H3; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77956329606     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100643t     Document Type: Article

References (39)

1. 3) of histamine receptor Nature 1983, 302, 832-837
2. 3-receptors Neuroscience 1985, 15, 553-562
3. 3-receptors Neuroscience 1987, 23, 149-157
4. Fink, K.; Schlicker, E.; Neise, A.; Gothert, M. Involvement of presynaptic H3 receptors in the inhibitory effect of histamine on serotonin release in the rat brain cortex Naunyn Schmiedeberg's Arch. Pharmacol. 1990, 342, 513-519
5. 3 receptors in the modulation of noradrenaline release from rat spinal cord slices Eur. J. Pharmacol. 1995, 287, 127-133
6. 3H]GABA release from depolarization-stimulated slices of rat substantia nigra pars reticulatta Neuroscience 1997, 80, 241-249
7. 3 receptor activation inhibits acetylcholine release from the guinea pig myenteric plexus Agents Actions 1991, 33, 167-169
8. 3 receptor antagonists go to clinics Biol. Pharm. Bull. 2008, 31, 2163-2181
9. Yokoyama, F.; Yamauchi, M.; Oyama, M.; Okuma, K; Onozawa, K.; Nagayama, T.; Shinei, R.; Ishikawa, M; Sato, Y.; Kakui, N. Anxiolytic-like profiles of histamine H3 receptor agonists in animal models of anxiety: a comparative study with antidepressants and benzodiazepine anxiolytic Psychopharmacology 2009, 205, 177-187
10. Ishikawa, M; Shinei, R; Yokoyama, F; Yamauchi, M; Oyama, M; Okuma, K; Nagayama, T; Kato, K; Kakui, N; Sato, T. Role of hydrophobic substituents on the terminal nitrogen of histamine in receptor binding and agonist activity: development of an orally active histamine type 3 receptor agonist and evaluation of its antistress activity in mice J. Med. Chem. 2010, 53, 3840-3844
11. 3 receptor agonist, 4-(1 H- imidazole-4-ylmethyl)piperidine J. Med. Chem. 1994, 37, 332-333
12. Garbarg, M.; Arrang, J. M.; Rouleau, A.; Ligneau, X.; Tuong, M. D. T; Schwartz, J. C.; Ganellin, C. R. S -[2-(4-Imidazolyl)ethyl]isothiourea, a highly specific and potent histamine H3 receptor agonist J. Pharmacol. Exp. Ther. 1992, 263, 304-310
13. 3 receptor and its ligands Prog. Med. Chem. 2001, 38, 279-308
14. 3 receptor explaining agonist and antagonistic activity simultaneously Arch. Pharm. (Weinheim, Ger.) 2000, 333, 254-260
15. Uveges, A. J.; Kowal, D.; Zhang, Y.; Spangler, T. B.; Dunlop, J.; Semus, S.; Jones, P. G. The role of transmembrane helix 5 in agonist binding to the human H3 receptor J. Pharmacol. Exp. Ther. 2002, 301, 451-458
16. 3 receptor agonist J. Med. Chem. 2004, 47, 2414-2417
17. Ishikawa, M.; Furuuchi, T.; Yamauchi, M.; Yokoyama, F.; Kakui, N.; Sato, Y. Synthesis and Structure-activity relationships of N -aryl-piperidine derivatives as potent (partial) agonists for human histamine H3 receptor Bioorg. Med. Chem. 2010, 18, 5441-5448
18. 3 receptor antagonists/agonists J. Med. Chem. 2004, 47, 2678-2687
19. 3 receptor lacking a nitrogen atom in the side chain J. Med. Chem. 2004, 47, 3264-3274
20. Kitbunnadaj, R.; Hoffmann, M.; Fratantoni, S. A.; Bongers, G.; Bakker, R. A.; Wieland, K.; el Jilali, A.; De Esch, I. J. P.; Menge, W. M. P. B.; Timmerman, H.; Leurs, R. New high affinity H3 receptor agonists without a basic side chain Bioorg. Med. Chem. 2005, 13, 6309-6323
21. 3 receptor agonists J. Med. Chem. 2008, 51, 2944-2953
22. http://sparc.chem.uga.edu/sparc/.
23. Hiral, S. H.; Karickhoff, S. W.; Carreira, L. A. A rigorous test for SPARC's chemical reactivity models: estimation of more than 4300 ionization pKas Quant. Struct.-Act. Relat. 1995, 14, 348-355
24. Barrow, J. C.; Nantermet, P. G.; Stauffer, S. R.; Ngo, P. L.; Steinbeiser, M. A.; Mao, S. S.; Carroll, S. S.; Bailey, C.; Colussi, D.; Bosserman, M.; Burlein, C.; Cook, J. J.; Sitko, G.; Tiller, P. R.; Miller-Stein, C. M.; Rose, M.; McMasters, D. R.; Vacca, J. P.; Selnick, H. G. Synthesis and evaluation of imidazole acetic acid inhibitors of activated thrombin-activatable fibrinolysis inhibitor as novel antithrombotics J. Med. Chem. 2003, 46, 5294-5297
25. Schreiber, J.; Maag, H.; Hashimoto, N.; Eschenmoser, A. Dimethyl(methylene)ammonium iodide Angew. Chem., Int. Ed. 1971, 10, 330-331
26. Ganem, B.; Ikota, N.; Muralidharan, V. B.; Wade, W. S.; Young, S. D.; Yukimoto, Y. Shikimate-derived metabolites. 11. A total synthesis of (A)-chorismic acid J. Am. Chem. Soc. 1982, 104, 6787-6788
27. Kan, T.; Fukuyama, T. Ns strategies: a highly versatile synthetic method for amines Chem. Commun. 2004, 353-359
28. 2). Formation and application to organic synthesis J. Am. Chem. Soc. 1965, 87, 1353-1364
29. Abraham, D. J. X-ray Crystallography and Drug Design. Computer-Aided Drug Design; Methods and Applications; Marcel Dekker: New York and Basel, Switzerland, 1989; pp 93-124.
30. 3 receptors Eur. J. Pharmacol. 2001, 433, 141-150
31. 3 receptor Biochem. J. 2001, 355, 279-288
32. Park, J. H.; Scheerer, P.; Hofmann, K. P.; Choe, H. W.; Ernst, O. P. Crystal structure of the ligand-free G-protein-coupled receptor opsin Nature 2008, 454, 183-188
33. Baldwin, J. M; Schertler, G. F. X; Unger, V. M. An alpha-carbon template for the transmembrane helices in the rhodopsin family of G-protein-coupled receptors J. Mol. Biol. 1997, 272, 144-164
34. Abad-Zapatero, C.; Metsz, J. T. Ligand efficiency indices as guideposts for drug discovery Drug Discovery Today 2005, 10, 464-469
35. Lin, J. H.; Liu, A. Y. H. Inhibition and induction of cytochrome P450 and the clinical implications Clin. Pharmacokinet. 1998, 35, 361-390
36. Newton, D. J.; Wang, R. W.; Lu, A. Y. Cytochrome P450 inhibitors. Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes Drug Metab. Dispos. 1995, 23, 154-158
37. Bjornsson, T. D.; Callaghan, J. T.; Einolf, H. J.; Fischer, V.; Gan, L.; Grimm, S.; Kao, J.; King, S. P.; Miwa, G.; Ni, L.; Kumar, G.; McLeod, J.; Obach, S. R.; Roberts, S.; Roe, A.; Shah, A.; Snikeris, F.; Sullivan, J. T.; Tweedie, D.; Vega, J. M.; Walsh, J.; Wrighton, S. A. The conduct of in vitro and in vivo drug-drug interaction studies: A PhRMA perspective J. Clin. Pharmacol. 2003, 43, 443-469
38. 3 receptor antagonists Bioorg. Med. Chem. Lett. 2006, 16, 989-994
39. Kansy, M.; Senner, F.; Gubernator, K. Physicochemical high throughput screening: parallel artificial membrane permeation assay in the description of passive absorption processes J. Med. Chem. 1998, 41, 1007-1010